The recently identified Lomaiviticins A and B have demonstrated potent DMA-damaging capabilities, as well as high cytotoxicity against a number of cancer cell lines. However, when compared to other known DNA-damaging anticancer drugs, their cytotoxicity profile differs. This indicates a unique mechanism of action. Researchers as of yet, have not been successful in elucidating their biological mechanism, nor have there been any reports on the synthesis of these complex molecules. Access to these molecules through chemical synthesis will allow for studies aimed at elucidation of their biological function. Initial synthetic studies will focus on accessing lomaiviticin B aglycon. We have proposed a synthesis which will access the target in eighteen steps. Key transformations include a Dotz benzannulation, a carbene electrocyclization and an oxidative enolate dimerization. Over the couse of our studies we will engage in indepth methodology studies on a unique stereoselective dimerization event which will afford the C2-symmetric molecule. [unreadable] [unreadable]